Flustra foliacea alkaloids

Morales-Rios, M.S., Suarez-Castillo, O.R., and Joseph-Nathan, P. (1999) General approach to the synthesis of marine bryozoan Flustra foliacea alkaloids total syntheses of debromoflustramines A and B. J. Org. Chem., 64,1086-1087. 

Peters, L Wright, A. D Kehraus, S., Giindisch, D., Tilotta, M. C. and Koning, G. M. 2004. Prenylated indole alkaloids from Flustra foliacea with subtype specific binding on NAChRs. Planta Medica, 70 883-886. 

Peters L, Wright AD, Kehraus S, Giindisch D, Tilotta MC, Konig GM (2004) Prenylated Indole Alkaloids from Flustra foliacea with Subtype Specific Binding on NAChRs. Planta Med 70 883... 

Several of the alkaloids from bryozoans can be considered to be indoles—Amathla alternata and Zoobotryon vertlcillatum contain simple indoles while Chartella papyracea, Flustra foliacea and Hinckstnojlus-tra denticulata give rise to more complex polycyclic compounds. 

The marine bryozoan Flustra foliacea collected in the North Sea has given rise to the isolation of a complicated mixture of alkaloids, twelve of which have so far been identified (32-36). The structures are depicted in Scheme 11 flustramine A (1)... 

Scheme 11. Alkaloids from the marine bryozoan Flustra foliacea. Structures numbered in Arabic originate from specimens from the North Sea and those with Roman numbers are from Canadian specimens. Flustrabromine (11) and 6-bromo-/Vb-methyl-/Vb-formyl-tryptamine (10) were isolated as an intimate mixture of Z and E geometrical isomers. The formulas are not intended to depict absolute stereochemistry.

Other comparable examples are known. The main alkaloid in a Nova Scotia collection of Flustra foliacea, dihydroflustramine C, is related to pseudophrynaminol from the skin of the myobatrachid burrowing frog Pseudophryne coriacea. Both classes of alkaloids are based on the 3a-prenyl pyrrolo[2,3- >]indole skeleton (31). 

One of two new alkaloids isolated from the marine bryozoan Flustra foliacea proves to be 6-bromo-Nj -formyl-Nj -methyl-... 

The bryozoon Flustra foliacea contains bromoindole alkaloids ( bryozoan alkaloids) with the physostig-mine skeleton this is also characteristic for a group of alkaloids from the calabar bean Physostigma veneno-sum) F. A, Cj.HjsBrN, Mr 389.38 F B, CjiHjsBrNj, Mr 389.38. 

From North Sea Bryozoan Flustra foliacea) several, brominated indole alkaloids have been isolated. These include deformylflustramine and flustramine. Deformylfrustrabromine A and deformylfrustrabromine B... 

WuLFF, P., J.S. Carle, and C. Christophersen Marine Alkaloids. Part 4. A Form-amide, Flustrabromine, from the Marine Bryozoan Flustra foliacea. J. Chem. Soc., Perkin Trans. I 1981, 2895. 

Figure 22.6 Examples of physostigmine alkaloids isolated from Flustra foliacea.

Carle, J.S. and Christophersen, C. (1979) Bromo-substituted physostigmine alkaloids from a bryozoa Flustra foliacea. J. Am. Chem. Soc., 101, 4012-4013. 

Holst, P.B., Anthoni, U., Christophersen, C., and Nielsen, P.H. (1994b) Marine alkaloids, 15. Two alkaloids, flustramine E and debromoflustramine B, from the marine bryozoan Flustra foliacea. J. Nat. Prod., 57, 997-1000. 

Keil, P., Nielsen, E.G., Anihoni, U., and Christophersen, C. (1986) Marine alkaloids, 11. Flustramide B and flustrarine B from the marine bryozoan Flustra foliacea. Synthesis of flustrarine B. Acta Chem. Scand., B40, 555-558. 

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